Brown azo dye and process of making same.



COLOR COMiANY, OF NEW YORK, H. Y.

BRGWN DYE No. erases Application tiled September 19071 Specification or" 1 3.1511? fflAItEzl.

Serial Ila 331336.

To all whom it may concern:

Be it known that I, Gnono Karrsonnn, a citizen of the German Empire, resident of Frsnki'orton-thei/Iain, Prussia, have invented new and useful Improvements in Brown Azo Dye and Processes of Making Same, of which the following is specification.

I have' found that valuable inonoazodyestu'ils are obtained by combining the diaminodiphenyiand dianiinophenylnaphthylethersulfonic acids of the formulae l l v I l OO ,H SO H o-o n,,so;.u with the diazo Compounds of 0-aminophenol derivatives. 1

The production of, dianiinophenylnaphthylether sulfonic acids has alreadybeen described in the French Patent No. 287,850; the diaminodiphenylether sulionic acids are obtained in an analogous manner by condensing dinitrochlorbenzene,with the phen olsulfonic acids in an aqueous solution in the presence of soda or caustic soda lye and reducing the nitro products so obtained.

The new coloring matters are represented by the following general formula X,N:N/\,/\O (wherein X signifies the radical of an ortho diazophenol and R an aroinatical radical as phenyl or naphthyl).

hey are dark powders dissolving in water with orange to brownish-red color, in concentrated sulfuric acid with orngc to bluish:

red color, and dye uni-non woo in brownislrorange to hrowzi arered shades,

which treated with hichromate are converted into full yellowish-brown shades, distinguished by their excellent i'astness to washing and milling and, in particular, by their unusual fastness to light.

The process is illustrated by the following examples:

Example 1. The diazo solution produced in the Well-known manner from 15. kilos pnitro-o-arninophenol, 36 kilos hydrochloric acid and 6.9 lril nitrite is allowed to run into a solution of kilos diaminophenylbota-uaphthylether6sulfonic acid (from 2.6 naphtholsullonic acid and dinitrochlorbenzene) presence of an excess of soda. The Whole is stirred for several hours in the cold, and after heating to O, the

coloring matter which has formed is precipitatod by common salt as a brown powder soluble water with on orange color and yields when dyed direct on wool a brownish orange shade, which by chroming is changed into a full yellowish-brown;

Example if in the foregoing example instead of the diurninophenyl-beta-naphthylether-ftsulionic acid 28 kilos diaminodiphe nylether-p-sulionic acid (from p-phenolsulionic acid and dinitrochlorbenzenel are used, a dyestull'v oi analogous properties is 0btained whichvdyes wool direct orange and the shade of, which. when after-chromed is quite yellowish-brown. In an analogous manner valuable dyestufl's with quite similar properties are obtained if in the above examples the p-nit'oo-a1ninophenol is replaced by the equivalent (niantity of another o-arninoplmnol derivate, as o-aniinophenol sulionic acid, nitroaininophenolsulfonic acid or pic-raininic acid, and if other diarninodiphenylor disminophenylnaphthylether sulfonio acids used.

What 3: claim. is

1. The process for the manufacture of inonoazo dyes which consists in combining oncmoleculo oi the diazo compound of an ortlioaininophenol derivative with one molecule ola dianiinodiohenylor diaminophenyln aphthylether sullonic acid of the formula origin,o.mrr cmc rcso ne cgn ne onur emc rrso ue substantially as described.

As new products the monoazo -dye stuts, thus ontan'iel, corresponding to the liNzNl/ ii li (1)llH (3)O.R.SO Na() (wherein X signifies the radical of an orthodiezophenol and it an aromatlcal radical as phcnyl ornaplithyl),bcu1g dark powders,sol

; able in water with orange to brownish-red @0101, soluble in concentrated sulfuric acid with omnge to red color, dyeing unmordented 'Wool in brovmish-orange to brownish-red shades changing into brown shades 5 by after-dimming, substantially as described.

In Witness whereof I have hereunto signed GEORG KALISCHER JEAN GRUND,

Witnesses:

CARL GRUND. 

